Dude looks like a lady
by WinchesterWeather
Summary: Where Dean's life is an Aerosmith song - or, Gabriel's not as dead as one might think - and he's got a few tricks up his sleeve. One of them involves turning our favorite brothers into girls. Can they handle it? How much harder can hunting be in their new female bodies? / temporary genderswap, mature content in later chapters, dean/cas and maybe some sam/gabriel
1. Chapter 1

**This is my first time starting a story on this website. Review if you liked it, please? If people do, I'll continue. :)  
**

* * *

The first thing he noticed when he woke up was the pressure on his chest. Being thrown against the ground was never particularly fun, but even more so this time for some reason.

The second thing was, Sam was gone, a female in his place. A dead ringer for Sam, almost. The two of them were in the motel room Dean had rented earlier - so where the hell was Sammy? He sighed and put a hand to his head, trying to gather recollection of the previous events.

And that's when he _noticed._

Not only was his hair…smooth, it was long, draping down a bit past his shoulders. He looked down, and if it happened to anyone but him, he'd laugh. He had a rack. _A rack._

"What the - _Gabriel!_" he shouted, suddenly remembering.

They were here on a case. Inmates started turning up dead in the prison cells. An abusive father died from being beat to death by his own deadbeat dad - who had died, twenty years prior. Sam had found candy wrappers at the scene. And now they were girls. It was all starting to make some sort of sick sense.

He flipped the female next to him over. "…Sam?"

After a bit of shaking, Sam's eyes opened. He pushed Dean off.

"Who are you?!"

He groaned. "Look down, dude."

"Wh-"

"Just…look down," Dean muttered.

It took Sam a minute, and he slowly pushed himself off. "…Dean?"

"The one and only," he said, before allowing Sam to pull him up. "I'm gonna fucking kill Gabriel."

"Why would he turn us into...girls?" Sam mutters, suddenly aware of his own lengthy hair. Not that it made much of a difference from when he was a guy.

"Why did he trap us in T.V. land? Why did he kill me a thousand times? The dude's whacko!"

It was quiet for a bit - neither of them knowing what to say - until Dean sniggered a bit.

"What?" Sam said, looking up.

"I always knew you'd make an ugly chick."

/

"I'm sorry, but I can't," Castiel said, looking at Sam. "Whatever Gabriel has done, it seems I am unable to fix it."

"Great," Dean called from the bathroom, "so we're stuck as Alexia and Hayley?"

"I don't understand that reference," Castiel grumbles.

"Alexia and Hayley traded places with each other. I have no idea who the hell we've traded with," Sam says, and he gestures down to his new body, and at the plaid shirt that's surprisingly tight due to a pair of DD-cup breasts.

"It seems this body is your own," Cas says, and he takes a seat on the motel bed beside Sam, "only altered slightly to a more…feminine degree."

Dean steps out of the bathroom, hair knotted as he'd been trying to figure out how to comb through it.

"Yeah? Well feminine degrees suck. Plus, Sam got the tits."

Dean looked down at his own body. A C-up at best, he thought. All the times he's looked at girls' breasts, he never realized how much of a pain these things were. None of his shirts fit anymore, he had settled for an oversized flannel overshirt that he'd never bothered to take back, and a pair of jeans that were falling down with his every move.

"I don't want them," Sam grumbles. "They're…they're sore."

Dean shakes his head and pops open the top to a beer. "Cas, you sure you can't use some of your angel mojo and poof our dicks back?"

Cas' eyes, for once, aren't on Dean's. They're aimed at the ground.

"My apologies," he says. "You're stuck in these forms until we can get Gabriel to change you back."

Sam's picking at his own clothing. His shirts are all suddenly too tight, and the normal jeans are chafing like hell. He groans inwardly at the thought of what he's about to say.

"We need to go shopping."

"Dude, did Gabriel change more than just your friggin' body? You sound like more of a chick than before," Dean retorts. Sam's fighting back an impulse to hit him.

"Dean, what do you think will happen if we go out like this, braless and in clothes that are tight in the wrong places?"

"I am _not_ wearing a bra," Dean grits.

"I must agree with Sam on this," Cas says, and if Dean didn't know the angel better, he'd say he almost looked flustered. "You're likely to have men leering at you every step you take if you go out like that."

He sighs, defeated, and mutters a 'fine' under his breath, pulling his flannel shirt over his chest as he opens the hotel door.

Shopping for bras can't be that hard, can it?


	2. Chapter 2

Getting fitted was probably one of the worst experiences of his life.

He had thought there was just a size for bras, like small medium and large, but oh god, no. If he feels one more measuring tape against his breasts, he's going to punch someone.

He feels like punching Gabriel just for having to say _his_ breasts. But he inevitably buys a bra - a black one, chic and produces a mass amount of cleavage, something he'd like a girl he'd get with to wear - and after a good fifteen minutes of trying, clamps it on. It's much easier to take one off than to put it on, he thinks.

Sam, apparently, had as much trouble as he did, because when he came out of the store and back to the meeting place, he was shuddering and groaning, "never again."

The day produces of mostly buying clothes. He had no idea what any of the sizes were, and it took him forever just to find things that fit.

He also wondered why girls didn't have any normal clothing in outlet stores. Guys - you want a V-neck t-shirt, that's cool. They're basic. But no, girls shopping is completely different. So many different styles and fabrics.

He ends up buying six pairs of jeans and about that many tops. It's not like he's never bought clothes for girls before. Buying them for himself in a girl's body, though, was beyond weird. He's hoping he's not stuck in this state long enough to go through all of the clothes he's bought, but he can't deny being just a bit…curious.

He admits to looking at himself naked in the mirror. Really, who wouldn't?

If you conducted a survey, he's sure, of what people would do had they been swapped genders, most people would say masturbate. He can't say he's never wondered.

Those thoughts should really vanish in his head when Castiel appears beside them, but unfortunately, they don't. They might, in fact, get worse.

"Hello," he says.

"Any luck on finding Gabriel?" Sam says.

"Wherever he is, he does not wish to be found," Cas mumbles. "I fear you might be stuck like this for some time."

That's not the answer they wanted to hear. Dean sighs.

"I hate these damned clothes," he grits. "I hate having tits."

He's even skinnier in this form, possibly even shorter and the worst thing is, girl or not, he still feels like himself.

Though his prized masculinity may be slipping.

He can hear his voice notably higher, though not as much as Sam's. He prays he doesn't run into anyone that he knows.

It's not all that hard to recognize them. Sam looks well, like Sam, only his hair is just to his shoulders and his face is a little thinner. He makes a pretty cute girl, but the thought of that disturbs Dean to the point of vomiting so he keeps his mind off of that.

Dean himself, looks pretty close too. His hair is the same color, just longer and layered. His lips are bigger but his eyes are still the same bright green and he still has the same awfully hidden freckles.

Hell, he'd bang himself.

The thoughts of masturbation are back in his head and he tries to shake them out as Sam brings up the topic of the hunt.

"Do you think he'll kill more people? Now that he knows we're onto him?"

"He's Gabriel. He lives to be a fucking asshat," Dean says. "He probably will, just to tease us."

"You're not…continuing the hunt like this, are you?" Cas asks. That brings up a problem they hadn't thought about.

"Why can't we?" Dean says back. "Just 'cause we're chicks doesn't mean we're weak."

"This isn't a matter of strength, Dean. You're obviously uncomfortable just being in this situation. It's going to be harder to promote a cover alias if you're not even sure of yourselves."

Sam looks at Dean for a bit. "Plus, we'd need to make new badges. And…get new suits."

More fittings. Fucking great.

"What are you suggesting, then?" Dean asks. "We just let the dick go around killing people?"

"We let Cas help," Sam says. "Do our work undercover, but not FBI-esque. It's a small town, people talk. How easy is it to get drunk guys at a bar to tell hot chicks everything they know?"

"Aw, Sammy, you really think I'm hot?" Dean feigns, and then he realizes Sam is serious.

"No. No, no way. I'm not going to hit on a dude. No, that's just wrong," Dean says. "No."

"But it's not really you," Sam says. "It's…Deanna."

"Actually, it is the two of you. Nothing has changed apart from a few added chromoso-"

"Not helping, Cas," Sam grits between his teeth. "Come on Dean, just like you did with Charlie and the security guard-"

"We agreed never to mention that again!" Dean hissed.

"Look, do you want to get Gabriel to change us back or not?" Sam snaps.

Dean sighs, realizing he's right. "Fine. But I'm not taking my clothes off. Or his."

/

Dean had never felt so much sympathy (possibly empathy) for porn stars and models now. Dresses…especially slutty ones, were probably the most uncomfortable thing he's ever put on.

It doesn't help that Cas stares just a bit longer than usual as he comes out of the dressing room.

"Man, this is fucking weird," Dean murmurs, pulling the dress down and re-examining himself in the mirror. God, did he have curves.

"I don't think so. I've seen several women wearing dresses of a similar fashion," Cas comments, and Dean rolls his eyes.

"Not the dress, dumbass, the whole being a chick thing," Dean says. He's suddenly aware how knotted his hair looked - the girls he's been with never mentioned how hard maintenance was - and feels well, just a bit self-conscious. Damn new girl hormones.

"I'm surprised you're this uncomfortable with it. I'd think someone like yourself would find a way to take advantage of this situation," Castiel says.

It takes Dean a minute to get what he's implying - especially because this is Cas - the virgin Cas, who's more awkward than anyone he's ever met, and now he's calling Dean out.

"Are you calling me a perv?" Dean asks, folding his arms. It looked a lot less girly when he was a dude.

"Are you denying that you are obsessed with fornication?"

"I'm not…I'm not obsessed," Dean huffs. "Name a man that doesn't like sex."

"There is such a thing as asexuality," Castiel adds. "And celibacy."

"And being junkless," Dean says. "Maybe that's why Gabe's pissed at us - he misses out on one of the natural wonders."

Castiel almost clenches his fists. "Despite what you believe, angels are not without sexual orientation. My abstinence when I first met you did not speak for the rest of my kind."

Dean was going to say something else, he was sure of it. He's not sure why his stupid new hormones chose to highlight that part of what Castiel said. "When you _first_ met me?"

Cas doesn't get a chance to reiterate. Sam's back, in a slightly less attention grabbing dress. Something you'd see a girl wearing in a bar, yeah, but more casual. Less flash.

He should've tried that out.

/

"I still don't see why I have to do this. Why can't Cas?" Dean says, looking nervously around the bar.

"In case you haven't noticed, Dean, Cas is a dude. He's also shit at socializing, not to mention practically hustling," Sam says. Cas almost looks hurt.

"Sorry, Cas," Sam says, a bit awkwardly. "I didn't mean-"

"My people skills are rusty," he says, something Dean's sure he's heard before. "And it's much easier to sell a ruse to someone who is sexually appealing."

"Exactly," Sam says. Dean's not sure how he's ignoring the last bit of that comment.

Sam picks one of the guys at the pool table. The guy looks a bit too nervous, like something's out to get him.

Dean picks a more easier target. The guy drowning himself in alcohol who almost looks as if he'd spill his troubles to any random stranger at this point.

He clears his throat and takes a deep breath.

"Hey," he says, pulling into the seat next to the man. "How's life?"

"Touchy subject," the man says, downing his probably tenth shot of the night. "Clint. You are…?"

"Deanna," he says, biting his tongue. God, he was going to kill Gabriel. "I'm staying in town for a few weeks. Was hoping to get a feel for the…locals."

He was going to wash his mouth out with holy water.

"This ain't a good town to stay in," Clint says, surprisingly sober. "We got evil in here."

"Evil?" he says. "A man like you? Scared? That's got to be something really evil."

He practically purred the last words and Dean's pretty sure he's going to throw up. Sam was right, he's a little _too_ good at this.

"People are gettin' their just desserts lately," Clint says.

"Just desserts?"

"Gettin' what's comin' to 'em. God's punishing 'em for their sins."

Oh, great, he picked the religious nut. He'd like to say this dude has nothing to worry about, God's a deadbeat dad, he's gotta look out for the angels. But he's supposed to be undercover, so he keeps his bias against religion to himself.

"What about you? What's your sin?"

Clint smiles, and downs the last shot. "Lust."

_Fuck_, Dean thinks. Turned him on too early.

He forces a small smile. "I think we all have that in us, Clint."

He tries to direct the conversation back towards just desserts, sins, the whole shebang, but Clint's on him before he can say anything else.

Dean really doesn't want the dude to get any closer, but he's probably drunk and unaware of what he's doing, so he doesn't want to hurt him either. Dean settles on knocking the shot glass over onto his lap.

Only, that makes drunk guys pissed.

Clint full on lunges at him now - out of rage rather than lust, damn the sinning bastard - and he finds himself confused. His limbs are…different, and he's not used to fighting with them. It's like using a gun your whole life and then being put in a sword fight.

He works on blocking the punches and slaps, hoping it'll cause some sort of ruckus. But it's a bar, and fights happen, and the music is blasting so loud he's certain no one can hear them. Suddenly he's pushed up against a corner and Clint's fist is three inches away from his face.

Damn, this is gonna hurt.


	3. Chapter 3

The punch doesn't come.

He squints his eyes open, and the setting is different. It's the motel room from earlier.

"Dean, are you alright?"

It's Cas, of course. _Who else?,_ he mutters under his breath.

"If I ever see a guy corner a girl in a bar again, I'm going to rip his nuts off," Dean says, gasping for breath almost.

Cas gives him a quizzical look. "Why didn't you fight back? The change of gender has no impact on your strength."

"It wasn't my strength," Dean says, plopping down on the bed. "I'm not used to fighting like this. I'm shorter and thinner and I have tits that make it hard to throw punches straight."

"So you thought it would be a good idea to let a stranger attack you to adapt to your newfound circumstances?" Cas says. He almost sounds personally offended, as if Clint had went after him instead.

"Dude, it just sort of…happened. That guy was like, twice my size. He probably woulda' kicked my ass if I still had a dick."

"I wasn't implying otherwise," Cas says. "You didn't think to get me or Sam to help you?"

Before he can say anything, Cas is invading even more of his personal space than before. "Oh. Your head, it's…"

Dean places two fingers up to his head. Blood. Cas goes to heal it, but Dean pulls back.

"I've taken a knock against the wall before, Cas. I don't need to rely on you to heal me every time I get a bump."

If looks could kill, he'd be dead within a second. The look goes on, and on, until Cas disappears and reappears with Sam at his side.

"Wha-what the hell, Cas?" Sam says, jerking his body forward. His eyes settle on Dean. "What the hell?"

"You need a better vocabulary," Dean mutters.

"What happened?"

"Hitting on guys to get them to talk to you? Not a good idea, Sammy," Dean said.

"Did you get anything?" Sam asked, deciding to talk about the head wound later.

"Guy was pretty shaken up. Part of town is convinced this is God's doing, punishing people for their sins."

Sam scoffs. "I heard the same story, but get this - one of the strippers in town's on trial. Apparently, some guy slapped her around outside, and she killed him."

"Apparently?"

"She swears that she didn't touch him, he flew back and every bone in his body just broke."

"Sounds like Gabriel," Cas says.

Dean dabbed at his forehead with a rag from the bathroom. "We can follow up on that tomorrow. Tonight, I'm going to get the hell out of this dress and get a much deserved four hours."

Sam looked down at his own. "We're never mentioning this to anyone else."

"Nope," Dean said. "Cas, you gonna book a room?"

"He can stay here," Sam said. "There's a pull-out couch. It's one less credit card we have to scam."

"I don't sleep," Cas says, but says nothing more to object.

Dean shakes his head. "Whatever. Don't watch me sleep, or I'll personally clip your wings off."

/

Getting out of the dress proved to be difficult.

It was so…tight. He'd never taken off a top he couldn't just shake off or pull off by the neck.

He heard rapping at the door.

"Damnit Sammy, give me a minute," he called.

"Dean, it's me," Cas said. "You've been in there a while. I was wondering if you were injured."

He sighed. "You try pulling a dress like this off."

"Was that a request for assistance?"

"No!" he hisses.

He pulls once again at the zipper and can feel the tightness squeeze all the air out of his lungs. "Fuck."

One last attempt, and his hands finally grasp the zipper and pull it down. I can breathe again, he thinks, halle-fucking-lujah, as he pushes it down to the floor.

He twists the shower controls, awkwardly trying to step in with his new limbs. God, this was weird. Like a game of middle school "Would you Rather" gone wrong.

Why the hell did Gabriel have to give him long hair? He can't get it to hold, especially with the shitty hotel shampoo. It keeps falling down along his waist in sticky, tangled clumps.

When he even thought about the notion of being a girl, it usually consisted of masturbation. Not ridiculously stringy wisps of hair that were out to get him.

There was another knock on the door, albeit a bit muffled by the water.

"Dude, you took long enough in the shower as a guy!" Sam calls. "Quit touching yourself and hurry up!"

/

Dean's still not used to this body. He "forgets" to throw the bra on this morning, wishing nothing to do with that uncomfortable hell unless it's absolutely necessary. He also forgets how uncomfortable his normal jeans are and settles on a pair of boxers that are probably too big in this form. His Zeppelin shirt is, too, but he figures he deserves some normality after last night.

"You are aware you're no longer male?" Cas asks, and a smirk almost plays at his lips. Dean can't tell if the son of a bitch is teasing or not.

"Yeah, and you're aware I don't care?" he mutters, grabbing a beer. "These clothes are better than the ones I had on last night. Where's Sammy?"

"Sam went to the coroner's office this morning. Another body has turned up."

"When did he make an ID for Samantha?" Dean mumbles, rubbing at his eyes.

"I believe when you spent two hours in the bathroom last night," Cas replies. "He laminated them this morning."

"Yeah, well, Sam's hair is the same length as normal. Mine's practically tripled," he groans. "Gabriel is gonna die."

"Perhaps the purpose of turning you into women was to strengthen your respect of the female gender."

"I respect chicks plenty. Or at least enough not to be turned into a plastic barbie."

Cas tilts his head slightly. "This version of you is flesh and blood, Dean. Your chromosomes have simply been altered. You still resemble your male appearance, even."

"God, my life's an Aerosmith song," Dean snarks.

Cas tilts his head even further. "I don't understand that reference."

Dean sighs. "When this is over, and I don't have rapunzel's hair, I'm going to educate you with some classic rock."

Cas almost smiles. "Rapunzel's hair was longer and much more blonde."

"…You're telling me Rapunzel was real?" Dean chokes, almost spitting out his beer.

"Of course," he says. "Not as portrayed in the fairy tales, however."

"My empathy," Dean murmurs. "Long hair is a bitch."

"It looks fair on you," Cas says. "Suits you, even."

He's not sure how to reply to that, but thankfully, he doesn't have to. The door swings open, and Sam comes in and lays a photo on the table without saying a word.

"What's this?" he says, picking it up. It's a picture of Clint, from the night before. A somewhat mutilated, beaten Clint, but still the same creep.

"Gabriel's most recent victim," Sam says. "Found dead around three hours after he was seen brawling with you."

"You thinkin' Gabriel did this?"

"It looks like it," Cas murmurs, looking over his shoulder. "I don't believe Gabriel recognized you as…Deanna."

"Looks like we've got some sort of a motive, too," Sam says. "All of the victims - people who abused people, hurt them. The abusive inmate who killed his wife, the pimp who attacked the stripper, and now, Clint."

"Basically, he's killing dicks. Like usual," Dean scoffs.

"It almost seems fair," Sam says. "None of these are one time offenders, either. Clint, apparently, had a habit of picking bar fights, especially with women."

"Yeah, well, fair or not, the dude's killing people. We gotta stop him," Dean says.

"Get our bodies back, at least," Sam says. He hops up, grabbing the keys to the Impala and his jacket that's now fairly oversized for him.

"Where are you off to?" Dean asks.

"Well, we know what his victims are, right? I've got a plan."

"What, you're gonna go piss off a pimp?"

"I'm going shopping."

Sam shuts the door without another word.

"Somehow I don't think Gabriel needed much to change Sam into a chick," Dean mutters, sipping on his beer.


End file.
